Hello Austen, I think this is what’s happening to you:

Error #1: You get the following message:

>>>
Select Serial Port could not open port 'COM4': FileNotFoundError(2, 'The system cannot find the file specified.', None, 2)

Or an equivalent message:

>>>
could not open port 'COM4': PermissionError(13, 'A device attached to the system is not functioning.', None, 31)

Unplug, and plug back your ESP board. Then, double-check that you’ve selected the right serial port in the Tools > Serial menu. Then, click the “Connect/disconnect” button to establish a serial communication. You should now be able to upload a new script or re-run new code.

This error might also mean that you have your serial port being used in another program (like a serial terminal or in the Arduino IDE). Double-check that you’ve closed all the programs that might be establishing a serial communication with your ESP board. Then, unplug and plug back your ESP board. Finally, restart the uPyCraft IDE – try to select the serial port in the Tools > Serial menu.

Let me know if you have the firmware flashed too.